WO2009148257A2 - Novel silicon-based compound, production method thereof, and organic light-emitting element employing the same - Google Patents

Abstract

The present invention relates to a silicon-based compound which, when used as an organic layer in an organic light-emitting element, and in particular as a hole-injection layer, hole-transport layer and/or electron-blocking layer, can improve characteristics of the element such as the thermal stability, the light-emission efficiency, the luminance, the current efficiency and the power efficiency. The present invention also relates to a production method of the compound and to an organic light-emitting element employing the compound

Description

Novel silicon-based compound, preparation method thereof and organic light emitting device using the same

The present invention can improve the thermal stability, the luminous efficiency, the luminance, the current efficiency, the power efficiency, etc. of the device when introduced into the organic layer of the organic light emitting device, in particular, the hole injection layer, the hole transport layer, and / or the electron blocking layer. The present invention relates to a silicon compound, a method of manufacturing the same, and an organic light emitting device using the same.

The organic light emitting device is a self-light emitting device using a principle that a fluorescent material emits light by recombination energy of holes injected from an anode and electrons injected from a cathode by applying a voltage.

Since the first development of electroluminescent (EL) devices by Tang in 1987, many kinds of materials for electroluminescent devices have been developed. However, the commercially available electroluminescent device has a low luminance when it is used for a long time and its durability is also lowered due to deterioration, and thus it is necessary to improve this.

In order to put the organic light emitting device into practical use, materials constituting the organic layer, in particular, the hole injection material and the hole transport material constituting the hole injection and transfer layer must be thermally and electrically stable. When a voltage is applied to the device, heat is generated in the device. In the case of materials having a low crystallization temperature, the heat may cause a rearrangement phenomenon, and in the part where the rearrangement occurs, destruction of the device due to deterioration is accelerated. Can shorten the service life. Therefore, it is preferable that the material which comprises the organic layer of an element maintains amorphousness, and it is so preferable that the glass transition temperature is high.

Conventional hole injection materials include CuPc, m-MTDATA, 2-TNATA, and the like. Since CuPc of the following Chemical Formula 1 is a metal complex, it is excellent in adhesion to the electrode (ITO), stable, and also excellent in hole mobility, and thus is preferable as a hole injection material, but has a disadvantage in that it absorbs light in the visible region. , Currently not used.

[Formula 1]

In addition, m-MTDATA of the following formula (2) has a glass transition temperature of about 78 ℃, thermal stability is poor, there is a problem of crystallization, its use is currently insignificant.

[Formula 2]

On the other hand, 2-TNATA of the following formula (3) has a glass transition temperature of about 108 ℃, it is possible to ensure the thermal stability to some extent, but it is not enough to be satisfied.

[Formula 3]

The present invention is a silicon-based compound having a high electrical stability and charge transport ability, high glass transition temperature and can prevent crystallization; And organic light emitting devices having excellent thermal stability, luminous efficiency, luminance, current efficiency, power efficiency, and the like.

The present invention provides a silicon compound represented by the following formula (4).

[Formula 4]

In Formula 4, n is an integer of 1 to 5;

R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, aryl having 5 to 30 carbon atoms, heteroaryl having 5 to 30 carbon atoms, Aryloxy having 5 to 30 carbon atoms, alkyloxy having 1 to 30 carbon atoms, arylalkyl having 5 to 30 carbon atoms, cycloalkyl having 5 to 30 carbon atoms, heterocycloalkyl having 5 to 30 carbon atoms, and a halogen element;

X ¹ to X ⁴ are each independently C ₅ ~ C ₃₀ aryl, C ₅ ~ C ₃₀ heteroaryl and

It is selected from the group consisting of, any one or more of X ¹ ~ X ⁴

Wherein Ar ¹ to Ar ⁴ are each independently C ₅ to C ₃₀ aryl or C ₅ to C ₃₀ heteroaryl.

In another aspect, the present invention provides a method for producing a silicon compound represented by the formula (4) characterized in that it comprises the step of reacting a compound of the formula (5) and a compound of the formula (6).

[Formula 5]

In Formula 5, Y ¹ ~ Y ⁴ are each independently selected from the group consisting of hydrogen, C ₅ ~ C ₃₀ aryl and C ₅ ~ C ₃₀ heteroaryl, any one or more of Y ¹ ~ Y ⁴ is hydrogen Is; n and R ¹ to R ⁴ are the same as defined in Formula 4;

[Formula 6]

In Chemical Formula 6, Z is a halogen element selected from the group consisting of F, Cl, Br, and I; Ar ¹ to Ar ⁴ are the same as defined in Formula 4.

The present invention also provides an organic light emitting device comprising (i) an anode, (ii) a cathode, and (iii) one or more organic material layers interposed between the anode and the cathode, and at least one of the one or more organic material layers. The layer of provides an organic light-emitting device characterized in that it comprises a silicon compound represented by the formula (4).

In this case, the layer including the silicon compound represented by the formula (4) is preferably at least one of a hole injection layer, a hole transport layer and an electron blocking layer.

When the silicon compound represented by the formula (4) of the present invention is used in an organic layer, in particular a hole injection layer, a hole transport layer and / or an electron blocking layer of an organic light emitting device, the light emitting performance of the device, in particular thermal stability, luminous efficiency, luminance, current efficiency , Power efficiency and the like can be improved.

1 is a cross-sectional view showing an example of an organic light emitting device structure according to the present invention.

2 is a graph showing the results of UV absorbance measurement of the compound of formula 4-a prepared in Example 1.

3 is a graph showing the results of UV absorbance measurement of the compound of formula 4-f prepared in Example 1.

4 is a graph showing the results of UV absorbance measurement of the compound of formula 4-g prepared in Example 1.

5 is a lifetime graph of the organic light emitting diodes manufactured in Example 8 and Comparative Example 3. FIG.

The present invention has a high electrical stability and charge transport ability, the glass transition temperature is high, silicon-based compound that can improve the thermal stability, luminous efficiency, brightness, current efficiency, power efficiency, etc. of the device when introduced into the organic layer of the organic light emitting device It characterized in that to provide.

Silicone compound according to the present invention is a compound represented by the following formula (4).

[Formula 4]

In Formula 4, n is an integer of 1 to 5;

R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, aryl having 5 to 30 carbon atoms, heteroaryl having 5 to 30 carbon atoms, Aryloxy having 5 to 30 carbon atoms, alkyloxy having 1 to 30 carbon atoms, arylalkyl having 5 to 30 carbon atoms, cycloalkyl having 5 to 30 carbon atoms, heterocycloalkyl having 5 to 30 carbon atoms, and halogen atoms;

X ¹ to X ⁴ are each independently C ₅ ~ C ₃₀ aryl, C ₅ ~ C ₃₀ heteroaryl and

It is selected from the group consisting of, any one or more of X ¹ ~ X ⁴

Wherein Ar ¹ to Ar ⁴ are each independently C ₅ to C ₃₀ aryl or C ₅ to C ₃₀ heteroaryl.

In addition, in the chemical formula of the present invention, Ar ¹ to Ar ⁴ may each independently form or may not form a fused aliphatic ring, a fused aromatic ring, a fused heteroaliphatic ring or a fused heteroaromatic ring with an adjacent group.

The silicon-based compound of Formula 4 may contain Si, N and the like to have excellent electrical stability and hole transport ability, and may have high glass transition temperature to prevent crystallization. Therefore, when the silicon compound of Formula 4 is introduced into the organic layer of the organic light emitting device, thermal stability, light emission efficiency, luminance, current efficiency, power efficiency, and the like of the device can be improved.

Examples of the silicon-based compound of Formula 4 according to the present invention include, but are not limited to, compounds of the following Chemical Formulas 4-a to 4-g.

[Formula 4-a]

[Formula 4-b]

[Formula 4-c]

[Formula 4-d]

[Formula 4-e]

[Formula 4-f]

[Formula 4-g]

On the other hand, the compound of Formula 4 may be obtained by reacting the compound of Formula 5 and the compound of Formula 6.

[Formula 5]

In Formula 5, n is an integer of 1 to 5; Y ¹ to Y ⁴ are each independently selected from the group consisting of hydrogen, C ₅ -C ₃₀ aryl and C ₅ -C ₃₀ heteroaryl, at least one of Y ¹ -Y ⁴ is hydrogen; R ¹ to R ⁴ are the same as defined in Formula 4.

[Formula 6]

In Formula 6, Z is a halogen element selected from the group consisting of F, Cl, Br, and I, Ar ¹ ~ Ar ⁴ are each independently C ₅ ~ C ₃₀ aryl or C ₅ ~ C ₃₀ heteroaryl .

The compound of Formula 5 is a compound of Formula 7 and HNY ¹ Y ² and HNY ³ Y ⁴ (wherein, Y ¹ ~ Y ⁴ are each independently hydrogen, C ₅ ~ C ₃₀ aryl and C ₅ ~ C ₃₀ hetero It is selected from the group consisting of aryl, any one or more of Y ¹ ~ Y ^{4 It} can be obtained by reacting with an amine compound. In this case, the HNY ¹ Y ² and HNY ³ Y ⁴ may be the same or different amine compounds.

[Formula 7]

In Formula 7, T ¹ and T ² are each independently a halogen element selected from the group consisting of F, Cl, Br, and I; n and R ¹ to R ⁴ are the same as defined in Formula 4.

In addition, the compound of Formula 6 may be obtained by reacting a compound of Formula 8 with a compound of Formula 9.

[Formula 8]

Z-Ar ^1- Z

In Formula 8, Z is a halogen element selected from the group consisting of F, Cl, Br, and I, Ar ¹ is C ₅ ~ C ₃₀ aryl or C ₅ ~ C ₃₀ heteroaryl.

[Formula 9]

In Formula 9, W is a halogen element selected from the group consisting of F, Cl, Br and I, Ar ² ~ Ar ⁴ is the same as defined in Formula 4. In this case, W is preferably a halogen element having a lower reactivity than Z in the formula (8).

The silicon compound according to the present invention may be prepared according to the above method, but this is only one example, and the present invention is not limited thereto and may be prepared through a similar compound or a similar process.

In addition, the present invention provides an organic light emitting device comprising such a silicon-based compound.

Specifically, the organic light emitting device according to the present invention is an organic light emitting device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer between the anode and the cathode, at least one of the at least one organic layer One layer is characterized by including the silicon-based compound of formula (4).

The organic material layer including the silicon compound of the present invention may be any one or more of a hole injection layer, a hole transport layer, an electron blocking layer, a light emitting layer, an electron transport layer and an electron injection layer. In particular, since the silicon compound according to the present invention has excellent hole transport ability, the silicon compound is preferably included in the organic light emitting device as a hole injection layer, a hole transport layer, and / or an electron blocking layer material.

1 is a cross-sectional view showing an example of an organic light emitting device structure according to the present invention, wherein the substrate 101, the anode 102, the hole injection layer 103, the hole transport layer 104, the light emitting layer 105, the electron transport layer ( 106 and the cathode 107 are sequentially stacked. The electron injection layer may be positioned on the electron transport layer 106, and the electron blocking layer may be positioned on the hole transport layer 104.

As described above, the organic light emitting device according to the present invention may not only have a structure in which an anode, at least one organic material layer, and a cathode are sequentially stacked, but an insulating layer or an adhesive layer may be inserted at an interface between the electrode and the organic material layer.

In the organic light emitting device according to the present invention, the organic material layer including the silicon compound of Formula 1 may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

The organic light emitting device according to the present invention may be manufactured by forming an organic material layer and an electrode using materials and methods known in the art, except that at least one layer of the organic material layer is formed to include the silicon compound of the present invention. have.

For example, the substrate 101 may be a silicon wafer, quartz or glass plate, metal plate, plastic film or sheet.

The anode 102 material may be a metal such as vanadium, chromium, copper, zinc, gold or an alloy thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO ₂ : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.

The cathode 107 material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO ₂ / Al, and the like, but are not limited thereto.

Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the present invention and the present invention is not limited by the following examples.

Preparation of Compound

Example 1 Preparation of the Compound of Formula 4-a

(1) Preparation of (4-bromophenyl) triphenylsilane

Scheme 1

After dissolving 21.9 g (92.7 mmol) of 1,4-dibromo benzene in 500 ml of Tetrahydrofuran, 64 ml (102 mmol) of 1.6 mol normal butyllithium dissolved in normal hexane were added dropwise at -78 ° C, followed by stirring for 1 hour. . 27.3 g (92.7 mmol) of chlorotriphenylsilane were added thereto, followed by stirring at the same temperature for 1 hour and at room temperature for 5 hours.

An ammonium hydroxide solution was added to the reaction mixture, stirred for 1 hour, and then extracted three times with ethyl acetate. The organic layer was recovered, dried over magnesium sulfate, and the residue obtained by evaporation of the solvent was separated and purified by silica gel column chromatography (ethyl acetate / normal hexane (1/3)) to give 31 g of (4-bromophenyl) triphenylsilane as a white solid (yield 80). %) Was obtained.

(2) Preparation of N4, N4'-di (naphthalen-1-yl) biphenyl-4,4'-diamine

Scheme 2

2 g (4.93 mmol) of 4,4'-diiodobiphenyl and 1.4 g (9.86 mmol) of naphthalene-1-amine were dissolved in toluene, and 0.20 g (0.20 mmol) of tris dibenzylidine acetone dipalladium was added under nitrogen. 1.20 g (12.44 mmol) of sodium butoxide and 0.09 g (0.39 mmol) of (t-bu) ₃ P were added thereto, and the reaction mixture was stirred under reflux for 4 hours.

The reaction mixture was then cooled to room temperature, poured onto a thin pad of silica, subjected to chromatography, and then washed with dichloromethane. In addition, the solvent was concentrated to remove the solvent, dissolved in 30 ml of dichloromethane, and slowly poured into 450 ml of methanol to give 1.7 g of solid N4, N4'-di (naphthalen-1-yl) biphenyl-4,4'-diamine (yield 80%). Got.

(3) Preparation of the target compound

Scheme 3

27 g (65 mmol) of (4-bromophenyl) triphenylsilane prepared in (1) above and 12.9 g of N4, N4'-di (naphthalen-1-yl) biphenyl-4,4'-diamine prepared in (2) ( 29.5 mmol) was dissolved in 500 mL of toluene, and 0.8 g (0.9 mmol) of Pd ₂ (dba) ₃ was added under nitrogen. To this, 7.1 g (74 mmol) of NaOBu ^t and 0.7 ml (1.8 mmol) of (t-Bu) ₃ P were added.

The reaction mixture was stirred under reflux for 5 hours, and the reaction was confirmed by TLC to terminate the reaction, and cooled to room temperature after the completion of the reaction. The reaction mixture was poured onto a thin pad of silica for short chromatography and washed with MC. The filtrate was distilled under reduced pressure to remove the solvent, and the residue was purified by silica gel column chromatography (dimethylchloride / normal hexane (1/3)) to give a compound as an off-white solid (N4, N4'-di (naphthalen-1-yl). ) -N4, N4'-bis (4- (triphenylsilyl) phenyl) biphenyl-4,4'-diamine) 25g (yield 80%) was obtained.

¹ H-NMR (300 MHz, CDCl 3): δ 7.93 (d, 2H), 7.87 (d, 2H), 7.76 (d, 2H), 7.54 (d, 12H), 7.46 (m, 4H), 7.38 (m, 30H), 7.11 (d, 4H), 6.98 (d, 4H).

GC-MASS (FAB): 1104.53 g / mol.

Example 2. Preparation of Chemical Formula 4-f

Scheme 4

5 g (27.1 mmol) of Benzidine and 27 g (65 mmol) of (4-bromophenyl) triphenylsilane were dissolved in 500 mL of toluene, and then 1.9 g (2.2 mmol) of Pd ₂ (dba) ₃ was added under nitrogen. 13 g (135.5 mmol) of NaOBu ^t and 1.7 ml (4.4 mmol) of (t-Bu) ₃ P were added thereto.

The reaction mixture was stirred under reflux for 8 hours, and the reaction was confirmed by TLC. The reaction mixture was cooled to room temperature after completion of the reaction. The reaction mixture was poured onto a thin pad of silica for short chromatography and washed with MC. The filtrate was distilled under reduced pressure to remove the solvent, and the residue was separated and purified by silica gel column chromatography (dimeltylchloride / normal hexane (1/3)) to obtain 23 g of a compound as an off-white solid (yield 56%).

¹ H-NMR (300 MHz, THF-D8): δ 7.46 (m, 24H), 7.38 (m, 36H), 7.33 (d, 8H), 7.28 (d, 8H), 6.56 (d, 8H).

GC-MASS (FAB): 1520.57 g / mol.

Example 3. Preparation of the compound of Chemical Formula 4-g

(1) Preparation of (3-bromophenyl) triphenylsilane

Scheme 5

(3-bromophenyl) triphenylsilane in a white solid state by the same method as in (1) of Example 1, except that 21.9 g (92.7 mmol) of 1,3-dibromo benzene was used instead of 1,4-dibromo benzene. 25 g (65% yield) was obtained.

(2) Preparation of the target compound

Scheme 6

After dissolving 5 g (27.1 mmol) of Benzidine and 44.9 g (108.6 mmol) of (3-bromophenyl) triphenylsilane in 800 mL of toluene, 1.9 g (2.2 mmol) of Pd ₂ (dba) ₃ was added under nitrogen. 13 g (135.5 mmol) of NaOBu ^t and 1.7 ml (4.4 mmol) of (t-Bu) ₃ P were added thereto.

The reaction mixture was stirred under reflux for 8 hours, and the reaction was confirmed by TLC, and the reaction mixture was cooled to room temperature after the reaction was terminated. The reaction mixture was poured onto a thin pad of silica for short chromatography and washed with MC. The filtrate was distilled under reduced pressure to remove the solvent, and the residue was separated and purified by silica gel column chromatography (dimeltylchloride / normal hexane (1/3)) to obtain 18 g of a compound as an off-white solid (yield 45%).

¹ H-NMR (300 MHz, THF-D8): δ 7.46 (m, 32H), 7.40 (m, 44H), 7.22 (d, 8H), 7.11 (t, 4H), 6.57 (d, 4H).

GC-MASS (FAB): 1520.57 g / mol.

Experimental Example 1 Evaluation of Optical and Thermal Properties of the Compound

The optical properties of the compounds obtained in Examples 1 to 3 were evaluated and shown in Table 1 and FIGS. 2 to 4, respectively. At this time, UV absorbance was measured in the state of Tetrahydrofuran solution.

In addition, the optical properties of the compounds obtained in Examples 1 to 3 are shown in Table 1, where Td is the result measured by TGA analysis and Tg by DSC analysis.

Table 1

.	Optical properties				Thermal properties
	Absorption wavelength	Emission wavelength	HOMO Energy Level	LUMO Energy Level	Melting point	Td	Tg
Example 1	349 nm	446 nm	5.20 eV	1.94 eV	370.2 ℃	553 ℃	131.1 ℃
Example 2	322nm	406 nm	5.48 eV	2.07eV	376.4 ℃	556 ℃	132.2 ℃
Example 3	346 nm	408 nm	5.32eV	2.05eV	264.7 ℃	525 ℃	131.8 ℃

As a result of the analysis, it was found that the silicone compounds according to the present invention have excellent thermal properties as well as optical properties, and are particularly stable at 500 ° C. or higher.

<Production of Organic Light-Emitting Element>

Example 4

The glass substrate coated with ITO (Indium tin oxide) to a thickness of 1500 Å was washed with distilled water ultrasonic waves. After the washing of distilled water, ultrasonic washing with a solvent such as isopropyl alcohol, acetone, methanol, and the like was dried and transferred to a plasma cleaner, and then the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum depositor.

On the thus prepared ITO (anode), the compound of formula 4-a was vacuum vacuum deposited to a thickness of 600 kPa to form a hole injection layer. NPB ( N , N- di (naphthalene-1-yl) -N , N- diphenylbenzidine), a hole transporting material, was vacuum deposited to a thickness of 150 위에 on the hole injection layer to form a hole transport layer, and a blue light emitting material thereon DS-H41 (Doosan Co., Ltd.) and DS-405 (Doosan Co., Ltd.) were vacuum deposited to a thickness of 300 kPa to form a light emitting layer. Alq3, which is an electron injection and transport material, was vacuum deposited on the emission layer to a thickness of 250 kPa to form an electron injection and transport layer. Further, LiF was sequentially deposited on the electron injection and transport layer in a thickness of 10 kPa, and aluminum (cathode) was vacuum deposited at a thickness of 2000 kPa to manufacture an organic light emitting device.

Comparative Example 1

An organic light-emitting device was manufactured in the same manner as in Example 4, except that 2-TNATA was used instead of the compound of Formula 4-a as the hole injection material.

Experimental Example 2 Performance Evaluation 1 of Organic Light-Emitting Element

For each organic light emitting device manufactured in Example 4 and Comparative Example 1, the luminous efficiency was measured at a current density of 10 mA / cm 2, and the results are shown in Table 2 below.

TABLE 2

.	Hole injection material	Luminance (cd / ㎡)	Color coordinates	Peak λ (nm)	Luminous Efficiency (cd / A)	Power efficiency (lm / W)
Example 4	Compound 4-a	693	0.149, 0.146	455	6.9	2.9
Comparative Example 1	2-TNATA	563	0.152, 0.157	455	5.6	3.3

As can be seen from the results of Table 2, when the silicon-based compound according to the present invention is used as the hole injection material of the organic light emitting device, the luminous efficiency can be improved by 19% or more, and the blue color can be more intensely exhibited. .

In addition, the silicon compound according to the present invention has high amorphousness and can be formed continuously without blocking the opening of the evaporation source during film formation, and thus has shown a very effective result in improving the production yield of the organic light emitting device.

Example 5

On ITO (anode), 2-TNATA was vacuum vacuum deposited to a thickness of 600 kPa to form a hole injection layer, and the compound of formula 4-a was vacuum deposited to a thickness of 150 kPa to form a hole transport layer thereon. On the hole transport layer, blue light emitting materials DS-H41 (Doosan Co., Ltd.) and DS-405 (Doosan Co., Ltd.) were vacuum-deposited to a thickness of 300 kW to form a light emitting layer, and Alq3 was deposited to a thickness of 250 kW on the light-emitting layer to form electrons. An injection and transport layer was formed. Further, LiF was sequentially deposited on the electron injection and transport layer in a thickness of 10 kPa, and aluminum (cathode) was vacuum deposited at a thickness of 2000 kPa to manufacture an organic light emitting device.

Example 6

An organic light-emitting device was manufactured in the same manner as in Example 5, except that the compound of Chemical Formula 4-a was deposited at a thickness of 200 Hz instead of 150 Hz.

Comparative Example 2

An organic light-emitting device was manufactured in the same manner as in Example 5, except that NPB was used instead of the compound of Formula 4-a as the hole transport material.

Experimental Example 3: Performance Evaluation 2 of Organic Light-Emitting Element

For each organic light emitting device manufactured in Examples 5, 6 and Comparative Example 2, the luminous efficiency at a current density of 10 mA / cm 2 was measured, and the results are shown in Table 3 below.

TABLE 3

.	Hole transport material	Luminance (cd / ㎡)	Color coordinates	Peak λ (nm)	Luminous Efficiency (cd / A)	Power efficiency (lm / W)
Example 5	Formula 4-a Compound (150 ')	748	0.160, 0.200	453	7.5	4.1
Example 6	Formula 4-a Compound (200 ′)	741	0.157, 0.179	452	7.4	3.8
Comparative Example 2	NPB	559	0.154, 0.171	452	5.6	3.1

As can be seen from the results of Table 3, when the silicon compound according to the present invention is used as the hole transporting material of the organic light emitting device, the luminous efficiency and power efficiency can be improved by 25% or more.

Example 7

On ITO (anode), 2-TNATA was vacuum vacuum deposited to a thickness of 600 kPa to form a hole injection layer, and NPB was vacuum deposited to a thickness of 100 kPa to form a hole transport layer. The compound of Formula 4-a was deposited thereon to a thickness of 50 kV to form an electron blocking layer. On the hole blocking layer, blue light emitting materials DS-H41 (Doosan Co., Ltd.) and DS-405 (Doosan Co., Ltd.) were vacuum-deposited to a thickness of 300 kW to form a light emitting layer, and Alq ₃ was vacuumed to a thickness of 250 kW on the light emitting layer. Evaporation to form an electron injection and transport layer. Further, LiF was sequentially deposited on the electron injection and transport layer in a thickness of 10 kPa, and aluminum (cathode) was vacuum deposited at a thickness of 2000 kPa to manufacture an organic light emitting device.

Example 8

An organic light-emitting device was manufactured in the same manner as in Example 7, except that NPB, which was a hole transporting material, was deposited at a thickness of 120 GPa instead of 100 GPa.

Comparative Example 3

An organic light-emitting device was manufactured in the same manner as in Example 7, except that the thickness of the hole transporting material NPB was deposited to 150 GPa and the electron blocking layer was not formed.

Experimental Example 4: Performance Evaluation of Organic Light-Emitting Element 3

For each organic light emitting device manufactured in Examples 7, 8 and Comparative Example 3, the luminous efficiency was measured at a current density of 10 mA / cm 2, and the results are shown in Table 4 below.

In addition, the lifespan of each organic light emitting device manufactured in Example 8 and Comparative Example 3 was measured at an initial luminance of 1000 cd / m 2, and the results are shown in FIG. 5.

Table 4

	Hole transport layer	Electronic floor	Luminance (cd / ㎡)	Color coordinates	Peak λ (nm)	Luminous Efficiency (cd / A)	Power Efficiency (lm / W)
Example 7	NPB (100Å)	Formula 4-a Compound (50 ')	637	0.153, 0.157	452	6.4	3.4
Example 8	NPB (120Å)	Formula 4-a Compound (50 ')	640	0.151, 0.153	453	6.4	3.5
Comparative Example 3	NPB (150Å)	-	559	0.154, 0.171	452	5.6	3.1

As can be seen from the results of Table 4, when the silicon compound according to the present invention is used as the electron blocking layer material of the organic light emitting device, the luminous efficiency can be improved by 13% or more, and the power efficiency can be improved. . In addition, due to the electron blocking effect, the exciton can emit light only in the light emitting layer, thereby improving color purity. In addition, as shown in the result of FIG. 5, when the silicon compound according to the present invention is used as the electron blocking layer material of the organic light emitting device, the life of the device can be improved by 15% or more. Therefore, the silicon compound according to the present invention was found to be effective as an electron blocking layer of the organic light emitting device.

Claims (6)

1. Silicone compound represented by the following formula (4):

   [Formula 4]

   

   In Formula 4, n is an integer of 1 to 5;

   R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, aryl having 5 to 30 carbon atoms, heteroaryl having 5 to 30 carbon atoms, Aryloxy having 5 to 30 carbon atoms, alkyloxy having 1 to 30 carbon atoms, arylalkyl having 5 to 30 carbon atoms, cycloalkyl having 5 to 30 carbon atoms, heterocycloalkyl having 5 to 30 carbon atoms, and a halogen element;

   X ¹ to X ⁴ are each independently C ₅ ~ C ₃₀ aryl, C ₅ ~ C ₃₀ heteroaryl and

   

   It is selected from the group consisting of, any one or more of X ¹ ~ X ⁴

   

   Wherein Ar ¹ to Ar ⁴ are each independently C ₅ to C ₃₀ aryl or C ₅ to C ₃₀ heteroaryl.
2. A method for preparing a compound of Formula 4, comprising reacting a compound of Formula 5 with a compound of Formula 6:

   [Formula 4]

   

   In Formula 4, n is an integer of 1 to 5;

   R ¹ to R ⁴ are each independently hydrogen, alkyl having 1 to 30 carbon atoms, alkenyl having 2 to 30 carbon atoms, aryl having 5 to 30 carbon atoms, heteroaryl having 5 to 30 carbon atoms, Aryloxy having 5 to 30 carbon atoms, alkyloxy having 1 to 30 carbon atoms, arylalkyl having 5 to 30 carbon atoms, cycloalkyl having 5 to 30 carbon atoms, heterocycloalkyl having 5 to 30 carbon atoms, and a halogen element;

   X ¹ to X ⁴ are each independently C ₅ ~ C ₃₀ aryl, C ₅ ~ C ₃₀ heteroaryl and

   

   It is selected from the group consisting of, any one or more of X ¹ ~ X ⁴

   

   Wherein Ar ¹ to Ar ⁴ are each independently C ₅ to C ₃₀ aryl or C ₅ to C ₃₀ heteroaryl;

   [Formula 5]

   

   In Formula 5, Y ¹ ~ Y ⁴ are each independently selected from the group consisting of hydrogen, C ₅ ~ C ₃₀ aryl, and C ₅ ~ C ₃₀ heteroaryl, at least one of which is hydrogen; n and R ¹ to R ⁴ are the same as defined in Formula 4;

   [Formula 6]

   

   In Chemical Formula 6, Z is a halogen element selected from the group consisting of F, Cl, Br, and I; Ar ¹ to Ar ⁴ are the same as defined in Formula 4.
3. According to claim 2, wherein the compound of Formula 5 is a compound of Formula 7 and HNY ¹ Y ² and HNY ³ Y ⁴ (wherein, Y ¹ ~ Y ⁴ are each independently hydrogen, C ₅ ~ C ₃₀ Aryl and C Method selected from the group consisting of ₅ to C ₃₀ heteroaryl, wherein at least one of Y ¹ ~ Y ⁴ is hydrogen) characterized in that it is prepared through the reaction of an amine compound of formula (4):

   [Formula 7]

   

   In Formula 7, T ¹ and T ² are each independently a halogen element selected from the group consisting of F, Cl, Br, and I; n and R ¹ to R ⁴ are the same as defined in Formula 4.
4. The method of claim 2, wherein the compound of Formula 6 is prepared through the reaction of a compound of Formula 8 with a compound of Formula 9.

   [Formula 8]

   Z-Ar ^1- Z

   In Formula 8, Z is a halogen element selected from the group consisting of F, Cl, Br, and I; Ar ¹ is C ₅ -C ₃₀ aryl or C ₅ -C ₃₀ heteroaryl;

   [Formula 9]

   

   In Formula 9, W is a halogen element selected from the group consisting of F, Cl, Br and I; Ar ² to Ar ⁴ are the same as defined in Formula 4.
5. An organic light emitting device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic layer interposed between the anode and the cathode,

   At least one layer of the at least one organic material layer is an organic light emitting device, characterized in that containing the silicon compound of claim 1.
6. The organic light emitting device of claim 5, wherein the layer including the silicon compound of claim 1 is at least one of a hole injection layer, a hole transport layer, and an electron blocking layer.

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